Acetone → Benzoxazole

HRID 728174Notes

Reaction equation

HRID 728174 reaction equation
CC1C=CN2C=C(CS)N=C2C=1.BrC[C:15]1[CH:16]=[CH:17][C:18]2[O:22][C:21](N(CC)C=O)=[N:20][C:19]=2[CH:28]=1.CC(C)=O.C(=O)([O-])[O-].[K+].[K+]>O>[O:22]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:28][C:19]=2[N:20]=[CH:21]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 15644575HCID 15644575, compoundHCID 15684679HCID 15684679, compound

Product 1

HCID 9228BenzoxazoleYield 125.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7-methylimidazo[1,2-a]pyridin-2-ylmethanethiol (1.5 g) and 5-bromomethyl-2-(N-ethylformamido)benzoxazole (2.9 g) in a solution of acetone (40 ml) and water (30 ml) was adjusted to pH 9-10 with saturated aqueous potassium carbonate solution under ice-cooling. The mixture was stirred for 2 hours at the same temperature and the isolated precipitate was collected by filtration to give 2-(N-ethylformamido)-5-(7-methylimidazo[1,2-a]pyridin-2-yl)methylthiomethyl]benzoxazole (1.53 g).

Workup

  1. temperaturecooling
  2. filtrationthe isolated precipitate was collected by filtration

Sources & evidence

ORD record
ord-c2e22cb5710c4c158111be7d632440e3
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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